Winter Winery Outfit Inspiration—15 Looks That Set the Mood Beautifully

There’s something especially charming about a winery visit in winter. The cooler air, muted vineyard views, and cozy tasting rooms set the scene for outfits that feel warm, textured, and intentionally layered. Winter winery outfits tend to lean into those details with pieces that are comfortable yet still refined.

Soft knits, structured jackets, tall boots, and neutral tones all work beautifully in this setting, creating looks that feel seasonally grounded without being overthought. Ahead is a curated collection of winter winery outfit ideas that capture that easy, understated style the season naturally encourages.

Fringe Sweater & Leather Midi Skirt

A cream fringed sweater adds soft movement against the sleek finish of a black leather midi skirt. Heeled ankle boots refine the look, while gold jewelry adds a clean, polished touch for a cozy yet elevated winter winery vibe.

Faux Fur Coat & Black Maxi Dress

Soft, plush faux fur brings a luxe contrast to the long, fitted black dress, giving the outfit a warm, dramatic edge. The brown belt adds dimension, and pointed boots elongate the silhouette. A mini designer bag and dark sunglasses round out the look with a chic, winter-winery finish.

Wool Jacket & Riding Boots

Rich brown riding boots anchor the look, paired with black leggings for a clean, streamlined base. The wool jacket brings a polished, tailored touch, while the soft white layer underneath lightens the palette. The mix of textures and warm neutrals creates an inviting, classic feel for a winter winery setting.

Houndstooth Coat & Denim Midi Skirt

A long houndstooth coat brings structure and warmth, layered effortlessly over a dark top and a denim midi skirt. The skirt’s clean, straight silhouette pairs well with heeled black boots, adding height and polish. The mix of classic prints and winter textures gives the outfit a relaxed yet refined feel for a day of wine tasting.

Textured White Gown & Faux Fur Wrap

A long, textured white gown creates a striking winter silhouette, balanced with a statement concho belt that adds Western-inspired detail. The faux fur wrap draped over the shoulders introduces warmth and richness, while the wide-brim hat gives the look a polished, rustic edge. A sleek black clutch completes the ensemble with understated elegance.

Cozy Knit Cardigan & Mini Skirt

A soft, oversized white cardigan brings a warm, relaxed feel, contrasted by a dark mini skirt for a touch of structure. Sheer tights add a subtle layer of texture, while tall brown boots ground the look with rustic charm. The combination feels inviting and fireside-ready, fitting for a winter winery setting.

Faux Fur Jacket & Cream Trousers

Deep chocolate faux fur brings a plush, dramatic layer to soft cream trousers, creating a rich winter contrast. The taupe turtleneck adds warmth without overwhelming the palette, while brown boots and a suede bag tie the earthy tones together. The overall look feels cozy, polished, and effortlessly suited for a cold-weather winery visit.

Shearling Vest & Cream Knit Set

A soft cream knit turtleneck and matching pants create an effortless, relaxed base, made cozier with a brown shearling vest layered on top. The mix of warm textures feels inviting against the snowy backdrop, while oversized sunglasses add a touch of modern polish. The look blends comfort and understated style, fitting for a laid-back winter winery moment.

Brown Jacket & Knee-High Boots

Warm brown tones set the mood here, with a soft knit top and structured jacket creating a cozy layered look. Light-wash jeans keep things casual, while tall suede boots add height and a polished, rustic edge. A dark leather bag and round sunglasses tie the palette together for an easy, winter-winery outfit.

Tweed Set & Patent Knee-High Boots

A matching grey tweed jacket and midi skirt create a refined, monochrome base with a subtle winter texture. The black turtleneck adds contrast and structure, while glossy patent boots bring a sleek, modern edge. The combination feels polished and understated, making it a chic choice for an evening winery setting.

Chunky Sweater & Satin Skirt

A soft oversized knit gives a cozy, rustic feel, contrasted beautifully with the fluid drape of a cream satin skirt. Western-style brown boots add grounded warmth, while the wide-brim hat ties the look into the countryside setting. The mix of textures creates an effortless blend of comfort and elegance for a winter winery day.

Off-Shoulder Knit Dress

A chunky grey off-shoulder sweater dress brings cozy texture with a soft, relaxed silhouette. The long sleeves and ribbed knit add warmth, while the exposed neckline gives the look a subtle touch of elegance. The overall vibe feels effortless and inviting, fitting for a laid-back winter winery afternoon.

Knit Cardigan Set & Wool Hat

Soft neutral tones shape this look, with a cozy button-front cardigan layered over a matching knit skirt for an easy, elongated silhouette. The wide-brim wool hat elevates the outfit with a touch of Western charm, while the plush cream handbag adds warmth and texture. The monochromatic palette keeps everything refined and winter-winery ready.

Cropped Wool Jacket & Leather Gloves

A rich brown cropped wool jacket sets a warm, structured base, accented by plush fur-trimmed sleeves for added depth. Sleek leather gloves elevate the look with a refined touch, while black leggings and tall boots keep the silhouette clean. The oversized cognac handbag ties the earthy tones together, creating a polished winter winery ensemble.

Shearling Aviator Jacket & Black Maxi Skirt

A cropped shearling aviator jacket adds warmth and structure, pairing cleanly with a fitted black maxi skirt for a sleek, elongated look. The monochrome base keeps the palette refined, while pointed black boots bring a sharp finish. A small black handbag and narrow sunglasses complete the outfit with understated sophistication.

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